Patent GB-760687-A (GB)
Title: Improvements in or relating to compositions for the treatment of growing plants
IPC: C07D493/08
Filed: 1953-03-25
Abstract: Exo-cis alkyl hydrogen 3,6-endoxohexahydrophthalic acid esters and salts thereof, in which the alkyl radical is a primary or secondary radical having 1 to 8 carbon atoms. are prepared by reacting equimolar quantities of exo-cis-3,6-endoxohexahydrophthalic anhydride and a primary or secondary saturated, monohydric, aliphatic alcohol and neutralizing the resulting acid esters with inorganic or organic bases.  In an example, exo-cis 3,6-endoxohexahydrophthalic anhydride was dissolved in boiling ethanol to which a few drops of HCl were added and maintained at boiling temperature for half-hour after which on cooling the mono ethyl ester crystallized out, a portion of which was dissolved in ethanol to which diisopropylamine was added when, on cooling, ethyl diisopropylammonium 3,6 - endoxohexahydrophthalate was precipitated.  Other portions of the mono ester were reacted with caustic soda and caustic potash to give respectively ethyl sodium 3,6 - endoxohexahydrophthalate and ethyl potassium 3,6 - endoxohexahydrophthalate.  In another example the monomethyl ester was produced by reacting exo-cis 3,6-endoxohexahydrophthalic anhydride with methanol from which by treating with diisopropylamine, sodium hydroxide and potassium hydroxide respectively methyl diisopropylammonium-, methyl sodium, and methyl potassium-, 3,6-endoxohexahydrophthalates are produced. In another example n-propyl hydrogen 3,6-endoxohexahydrophthalate produced by refluxing exo - cis - 3,6 - endoxohexahydrophthalic anhydride in n-propanol, cooling and distilling under reduced pressure is subsequently treated with respectively diisopropylamine, sodium hydroxide and potassium hydroxide to produce n-propyl diisopropylammonium-, n-propyl sodium-, and n-propyl potassium 3,6-endoxohexahydrophthalates. Numerous other salts are mentioned including polyvalent metal salts, ammonium salts and other amine salts, e.g. mono-, di- and tri-alkyl amine and alkanol amine salts and mixed alkyl-alkanol amine salts.ALSO:Plant response e.g. root stimulant compositions comprise as the active component at least one compound which in the presence of water yields anions of exo-cis alkyl hydrogen 3, 6-endoxohexahydrophthalate the alkyl radical being a primary or secondary alkyl radical having from 1 to 8 carbon atoms and a finely divided solid carrier or viscous liquid carrier, or a pasty carrier or an emulsifying dispersing or wetting agent or a humectant.  The compound may be the acid per se or the water soluble salts e.g. of sodium, potassium, calcium, strontium, magnesium, aluminium, iron, cobalt, nickel, zinc, cadmium, mercury, copper, ammonium, mono-, di-, and trialkylammonium preferably having 1 to 12 carbon atoms in each alkyl radical the totality of carbon atoms preferably not being more than 12, mono-, di-, and trialkanolammonium salts preferably having from 2 to 3 carbon atoms in each alkanol group, and mixed alkyl-alkanolammonium salts preferably having from 1 to 4 carbon atoms in each alkyl group and from 2 to 3 carbon atoms in each alkanol group which are N-substituted in the ammonium radical by from 2 to 3 radicals of the type indicated.  The composition may be admixed with liquid and solid carriers such as water, oil, clay e.g. Fuller's earth, pyrophyllite, talc, bentonite, kieselguhr, diatomaceous earth, commercial clays such as Homer Clay and Tripoli, non-clay carriers e.g. sulfur, volcanic ash, calcium carbonate, lime, by-product lignin, lignocellulose, flour such as wood, walnut shell, wheat, soybean, potato, cotton seed.  The mixture may be dissolved, dispersed, suspended or emulsified in the liquid carriers and used as a spray, specified emulsifying or dispersing agents being long chain alcohol sulphates, such as sodium laurylsulphate, aliphatic or aromatic sulphonates, such as sulphonated castor oil or the various alkaryl-sulphonates (such as the sodium salt of monosulphonated nonyl naphthalene), and nonionic types such as the high molecular weight alkyl polyglycolethers or analogous thioethers, such as the decyl, dodecyl, and tetradecyl polyglycolethers and thioethers containing from 25 to 75 carbon atoms.  There may also be added fungicides, insecticides, bactericides and humectants examples of the latter being glycerine, diethylene glycol, ethylene glycol, polyethylene glycols generally, and water-soluble sugars and sugar-containing mixtures, such as glucose, fructose, galactose, mannose, arabinose, xylose, sucrose, maltose, lactose, raffinose, trehalose, dextrins such as white dextrin, canary dextrin, British gum &c., honey, molasses, maple syrup, maple sugar, and starch syrups such as corn syrup.ALSO:Herbicidal, defoliant and like plant response compositions comprise as the active component at least one compound which in the presence of water yields anions of exo-cis alkyl hydrogen 3, 6 - endoxohexahydrophthalate the alkyl radical being a primary or secondary alkyl radical having from 1 to 8 carbon atoms and a finely divided solid carrier or viscous-liquid carrier, or a pasty carrier, or an emulsifying, dispersing or wetting agent or a humectant.  The compound may be the acid per se or the water soluble salts e.g. of sodium, potassium, calcium, strontium, magnesium, aluminium, iron, cobalt, nickel, zinc, cadmium, mercury, copper, ammonium, mono -, di -, and trialkylammonium preferably having 1 to 12 carbon atoms in each alkyl radical the totality of carbon atoms preferably not being more than 12, mono -, di -, and trialkanolammonium salts preferably having from 2 to 3 carbon atoms in each alkanol group, and mixed alkyl-alkanolammonium salts preferably having from 1 to 4 carbon atoms in each alkyl group and from 2 to 3 carbon atoms in each alkanol group which are N - substituted in the ammonium radical by from 2 to 3 radicals of the type indicated.  The composition may be admixed with liquid and solid carriers and in the case of the former used as a spray when dissolved, dispersed, suspended or emulsified therein.  Wetting agent humectants, fungicides, insecticides, bactericides or other types of plant response agents may also be included.